ES2600636T3 - Spiro- [1,3] -oxazines and spiro- [1,4] -oxazepines as inhibitors of BACE1 and / or BACE2 - Google Patents

Spiro- [1,3] -oxazines and spiro- [1,4] -oxazepines as inhibitors of BACE1 and / or BACE2 Download PDF

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ES2600636T3
ES2600636T3 ES12724116.4T ES12724116T ES2600636T3 ES 2600636 T3 ES2600636 T3 ES 2600636T3 ES 12724116 T ES12724116 T ES 12724116T ES 2600636 T3 ES2600636 T3 ES 2600636T3
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alkyl
group
spiro
hydrogen
halogen
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Robert Narquizian
Emmanuel Pinard
Wolfgang Wostl
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F Hoffmann La Roche AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/537—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines spiro-condensed or forming part of bridged ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/20—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Compuesto de fórmula I:**Fórmula** en la que: V es -CR7aR7b-, W es -CR2aR2b-, X es -CR1aR1b-, -O-, -S- o -SO2-, Y -NH-C>=O-, Z se selecciona de entre el grupo que consiste de: i) heteroarilo, ii) heteroarilo sustituido con 1 a 4 sustituyentes seleccionados individualmente de entre R8, iii) arilo, y iv) arilo sustituido con 1 a 4 sustituyentes seleccionados individualmente de entre R8, R1a se selecciona de entre el grupo que consiste de: i) hidrógeno, ii) halógeno, y iii) alquilo-C1-6, R1b se selecciona de entre el grupo que consiste de: i) hidrógeno, ii) halógeno, y iii) alquilo-C1-6, R2a se selecciona de entre el grupo que consiste de: i) hidrógeno, y ii) alquilo-C1-6, R2b se selecciona de entre el grupo que consiste de: i) hidrógeno, ii) arilo, y iii) alquilo-C1-6, o R2a y R2b conjuntamente con el C al que se encuentran unidos forman un heterociclilo, R3 es F, R4 es F, R5 es H, R6 es H, R7a se selecciona de entre el grupo que consiste de: i) hidrógeno, y ii) alquilo-C1-6, R7b se selecciona de entre el grupo que consiste de: i) hidrógeno, y ii) alquilo-C1-6, R8 se selecciona de entre el grupo que consiste de: i) ciano, ii) ciano-alquilo C1-6, iii) halógeno, iv) halógeno-alcoxi C1-6, v) halógeno-alquilo C1-6, vi) alcoxi-C1-6, vii) alcoxi C1-6-alquilo C1-6, viii) alquinilo C2-6, y ix) alquilo-C1-6, n es 0 ó 1, m es 0 ó 1; p es 0 ó 1, o sales farmacéuticamente aceptables de los mismos.Compound of formula I: ** Formula ** in which: V is -CR7aR7b-, W is -CR2aR2b-, X is -CR1aR1b-, -O-, -S- or -SO2-, Y -NH-C> = O-, Z is selected from the group consisting of: i) heteroaryl, ii) heteroaryl substituted with 1 to 4 substituents individually selected from R8, iii) aryl, and iv) aryl substituted with 1 to 4 substituents individually selected from R8, R1a is selected from the group consisting of: i) hydrogen, ii) halogen, and iii) C1-6 alkyl, R1b is selected from the group consisting of: i) hydrogen, ii) halogen , and iii) C1-6 alkyl, R2a is selected from the group consisting of: i) hydrogen, and ii) C1-6 alkyl, R2b is selected from the group consisting of: i) hydrogen, ii ) aryl, and iii) C1-6 alkyl, or R2a and R2b together with the C to which they are attached form a heterocyclyl, R3 is F, R4 is F, R5 is H, R6 is H, R7a is selected from the group consisting of: i) hydrogen, and ii) C1-6 alkyl, R7 b is selected from the group consisting of: i) hydrogen, and ii) C1-6 alkyl, R8 is selected from the group consisting of: i) cyano, ii) cyano-C1-6 alkyl, iii) halogen, iv) halogen-C1-6 alkoxy, v) halogen-C1-6 alkyl, vi) C1-6 alkoxy, vii) C1-6 alkoxy-C1-6 alkyl, viii) C2-6 alkynyl, and ix) C1-6 alkyl, n is 0 or 1, m is 0 or 1; p is 0 or 1, or pharmaceutically acceptable salts thereof.

ES12724116.4T 2011-05-27 2012-05-24 Spiro- [1,3] -oxazines and spiro- [1,4] -oxazepines as inhibitors of BACE1 and / or BACE2 Active ES2600636T3 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP11167835 2011-05-27
EP11167835 2011-05-27
PCT/EP2012/059688 WO2012163790A1 (en) 2011-05-27 2012-05-24 Spiro-[1,3]-oxazines and spiro-[1,4]-oxazepines as bace1 and/or bace2 inhibitors

Publications (1)

Publication Number Publication Date
ES2600636T3 true ES2600636T3 (en) 2017-02-10

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ES12724116.4T Active ES2600636T3 (en) 2011-05-27 2012-05-24 Spiro- [1,3] -oxazines and spiro- [1,4] -oxazepines as inhibitors of BACE1 and / or BACE2

Country Status (22)

Country Link
US (1) US9079919B2 (en)
EP (1) EP2714697B1 (en)
JP (1) JP2014515382A (en)
KR (1) KR20140048137A (en)
CN (1) CN103596961B (en)
AU (1) AU2012264875B2 (en)
BR (1) BR112013030281A2 (en)
CA (1) CA2833813A1 (en)
CL (1) CL2013003372A1 (en)
CO (1) CO6801773A2 (en)
CR (1) CR20130580A (en)
EA (1) EA024286B1 (en)
EC (1) ECSP13013048A (en)
ES (1) ES2600636T3 (en)
IL (1) IL229334A (en)
MA (1) MA35191B1 (en)
MX (1) MX2013013910A (en)
PE (1) PE20141205A1 (en)
SG (1) SG194835A1 (en)
UA (1) UA111847C2 (en)
WO (1) WO2012163790A1 (en)
ZA (1) ZA201308395B (en)

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Publication number Publication date
AU2012264875A1 (en) 2013-10-31
ZA201308395B (en) 2014-07-30
SG194835A1 (en) 2013-12-30
UA111847C2 (en) 2016-06-24
EP2714697B1 (en) 2016-08-31
PE20141205A1 (en) 2014-09-22
IL229334A (en) 2017-02-28
EP2714697A1 (en) 2014-04-09
CO6801773A2 (en) 2013-11-29
WO2012163790A1 (en) 2012-12-06
IL229334A0 (en) 2014-01-30
ECSP13013048A (en) 2014-01-31
EA201391752A1 (en) 2014-04-30
US9079919B2 (en) 2015-07-14
CA2833813A1 (en) 2012-12-06
CL2013003372A1 (en) 2014-07-25
JP2014515382A (en) 2014-06-30
CR20130580A (en) 2013-12-09
NZ616817A (en) 2015-12-24
AU2012264875B2 (en) 2017-04-27
CN103596961A (en) 2014-02-19
MX2013013910A (en) 2014-01-24
MA35191B1 (en) 2014-06-02
BR112013030281A2 (en) 2016-11-29
CN103596961B (en) 2016-09-28
KR20140048137A (en) 2014-04-23
EA024286B1 (en) 2016-09-30
US20120302549A1 (en) 2012-11-29

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